Plugged for the Day
The morning light filtered through the sheer curtains of their bedroom, casting a soft glow over the neatly arranged space. The air held a faint trace of jasmine, a scent that always lingered when Claire was in control. For James, that fragrance was both a comfort and a signal—an unspoken promise of what was to come. Today, it hung heavier, laced with an undercurrent of authority that made his pulse quicken. Claire stood at the foot of the bed, her dark eyes gleaming with purpose as she surveyed him. Her lips curved into a subtle, knowing smile.
“Strip,” she said simply, her voice low but firm, leaving no room for hesitation.
James swallowed, his throat tight with anticipation. He shed his plain cotton pajamas, letting them pool on the hardwood floor. The cool air brushed against his bare skin, raising goosebumps as he stood vulnerable before her. Claire’s gaze never wavered, appraising him like a sculptor assessing raw clay. She stepped closer, her silk robe whispering against her thighs, and handed him a small, delicately wrapped package tied with a black satin ribbon.
“Open it,” she instructed, her tone carrying a hint of mischief.
His fingers trembled slightly as he untied the ribbon and peeled back the tissue paper. Inside lay a pair of lacy black panties, their design both elegant and provocative. The front was a soft, sheer lace that would cradle his manhood with a teasing caress, but the back was daringly open, leaving his rear exposed. He looked up at Claire, his cheeks warming.
“Put them on,” she said, her voice a velvet command.
James stepped into the panties, the fabric sliding smoothly over his hips. The lace hugged him snugly, the openness at the back making him acutely aware of his vulnerability. Claire nodded approvingly, then turned to the dresser, where a carefully curated collection awaited. She returned with a full-coverage black bra, its cups structured to hold the breast forms she’d chosen for him. The bra was practical yet sensual, its satin finish gleaming faintly in the morning light.
“Lift your arms,” she said, and he obeyed, letting her fasten the bra around his chest. The weight of the breast forms settled into place, their realistic heft pulling slightly at the straps. James shifted, adjusting to the unfamiliar sensation, his reflection in the nearby mirror catching his eye—a glimpse of a figure that was both him and not him.
Next came the stockings, sheer black nylon that shimmered as Claire handed them to him. He sat on the edge of the bed, rolling them carefully up his legs, the silky material clinging to his skin. They stopped just at the tops of his thighs, the elastic bands gripping gently but firmly. The sensation was electric, each movement sending a shiver through him as the fabric brushed against his skin.
Claire stepped back, her eyes narrowing as she considered her work. “Now the skirt,” she said, retrieving a sleek black pencil skirt from the closet. She held it out, and James stepped into it, the fabric gliding over his stockinged legs. Claire zipped it up, the skirt hugging his hips and tapering down to just above his knees, accentuating the curve of his borrowed silhouette. The hem brushed against the tops of his stockings, a constant reminder of the delicate balance between concealment and exposure.
“And this,” she said, presenting a cream-colored blouse, its fabric soft and slightly sheer. James slipped his arms into the sleeves, the blouse draping elegantly over the bra, the breast forms giving him a feminine contour. Claire buttoned it for him, her fingers deft and precise, her touch lingering just long enough to make his breath catch.
She stepped back, tilting her head as she studied him. “Almost there,” she murmured, then crossed to her vanity, returning with a shoulder-length wig of dark chestnut curls. The hair was glossy, the waves catching the light as she settled it onto his head, adjusting it until it framed his face perfectly. She tucked a stray curl behind his ear, her fingers brushing his cheek.
“Now, the face,” Claire said, her voice softening but still carrying that unshakable authority. She led him to the vanity, where an array of makeup awaited. James sat, his heart pounding as Claire worked with practiced ease. She started with foundation, smoothing it over his skin to create a flawless canvas. Blush followed, a soft rose that warmed his cheeks. Her brush danced over his eyelids, layering smoky shadow and a precise flick of eyeliner that made his eyes pop. Finally, she painted his lips a deep berry red, the glossy finish drawing attention to the curve of his mouth.
James stared at his reflection, barely recognizing the woman looking back. The wig framed his face in soft waves, the makeup accentuating features he’d never thought to highlight. The blouse and skirt hugged his body, the breast forms and stockings completing the illusion. He felt a strange mix of vulnerability and power, as if he were both exposed and invincible under Claire’s gaze.
“Stand,” she said, stepping back to admire her creation. James rose, the stockings whispering against his thighs, the lace of the panties shifting slightly. The weight of the breast forms pulled at his chest, grounding him in this new persona. Claire circled him, her heels clicking softly on the floor, her eyes gleaming with satisfaction.
“Now,” she said, her voice dropping to a husky whisper, “bend over the bed.”
James’s breath hitched, but he obeyed, leaning forward until his hands rested on the mattress, the pencil skirt stretching taut across his hips. Claire moved behind him, her fingers brushing the hem of the skirt before slowly sliding it up, the fabric bunching around his waist. The open-backed panties left him exposed, the cool air kissing his skin. He heard the soft click of a bottle opening, then felt the slick chill of water-based lube as Claire’s fingers found his eager entrance.
She worked slowly, deliberately, her touch both clinical and intimate. James bit his lip, a soft whimper escaping as her fingers prepared him, the sensation both invasive and exhilarating. Then came the butt plug, its smooth silicone surface cool against his skin. Claire pressed it gently but firmly, and James felt the initial stretch, a sharp but fleeting discomfort that gave way to a deep, satisfying fullness as the plug settled into place. The tapered base locked it securely, and he felt the tickle of the silicone tail—long, soft strands that mimicked a horse’s tail, cascading down from the plug to brush against his thighs.
Claire gave the plug a gentle tug, ensuring it was secure, and James let out a quiet moan, the sound involuntary but undeniable. The tail swayed slightly, its strands teasing the backs of his legs, a constant reminder of the intrusion filling him. Claire smoothed the skirt back down, the fabric sliding over his hips to conceal the plug and its tail, though he could still feel it swaying just above the hem.
“Stand,” she said again, and he did, his legs trembling slightly. The plug shifted inside him with every movement, a subtle pressure that sent waves of pleasure through him. The tail brushed against his stockings, a soft, tickling sensation that heightened his awareness of his transformed state.
James’s breath came in short, shallow bursts, his body thrumming with a mix of arousal and nervous excitement. The plug would be a constant presence, its weight and the gentle sway of the tail amplifying his awareness of his submission. He nodded, unable to find words, his mind already racing with the thought of stepping out into the world like this—feminine, exposed, and utterly under Claire’s control.
Claire stepped closer, her hand resting lightly on his hip. “Today,” she said, her voice low and commanding, “you’re going to run errands for me. As her.” She gestured to his reflection in the mirror, the woman he’d become under her guidance. “The plug stays in all day, and that tail will remind you of who you are. Every step, every moment, you’ll feel it. You’ll know it’s there, filling you, teasing you, while you do my bidding.”
She handed him a small list, written in her elegant script. “Groceries, dry cleaning, and a stop at the post office,” she said. “You’ll do it all as my perfect girl, won’t you?”
“Yes, Claire,” he managed, his voice soft, tinged with the same eagerness he felt pulsing through him.
She smiled, a glint of pride in her eyes. “Good. Now go. And don’t you dare disappoint me.”
James took a deep breath, smoothing the skirt over his hips, feeling the tail shift slightly as he moved.
Out You Go for Some Errands
James stood in front of the full-length mirror in their bedroom for a moment longer, his reflection a blend of familiarity and strangeness. The pencil skirt hugged his hips, the blouse draped softly over the breast forms, and the wavy dark chestnut wig framed his made-up face. The plug nestled securely inside him, its silicone tail swaying gently with every subtle shift of his weight, a constant, teasing reminder of Claire’s dominance. He could feel the fullness, the way it pressed against him, sending ripples of anticipation through his body. His heart raced, not just from the transformation, but from the knowledge of what lay ahead—stepping out into the world as her creation.
Claire watched him from the doorway, her arms crossed, a satisfied smile playing on her lips. “You’re almost ready,” she said, her voice smooth and commanding. She walked over to the closet and pulled out a pair of low block heels—black, sensible, with a three-inch lift that was modest enough not to scream for attention but high enough to alter his gait. “These will do nicely. They’ll make your hips sway just a little, enough to feel it, but not enough to turn heads unnecessarily.”
“Walk for me,” Claire instructed, her eyes gleaming.
He took a tentative step, then another, feeling the way the heels forced a subtle roll in his hips, a feminine sway that made the skirt brush against his thighs and the tail tickle the backs of his legs. The plug shifted with each movement, a deep pressure that made his breath catch.
He strode across the room, the heels clicking softly on the hardwood floor. The sway was there, undeniable, making him feel exposed even in the privacy of their home. The stockings whispered against each other, the lace panties cradling his manhood while leaving his rear open to the plug’s intrusion. He turned at the end of the room, facing her, his cheeks flushed beneath the makeup.
“Perfect,” she murmured. “Now, one last touch.” She reached for a bottle on the dresser—a musky perfume, its scent heavy and intoxicating, with notes of amber and vanilla that screamed sensuality. She spritzed him heavily, first on his neck, then his wrists, and finally a generous mist over his chest and skirt. The fragrance enveloped him, clinging to his skin and clothes, making him smell like desire incarnate. “There,” she said, stepping back. “Now you’ll smell extra slutty while you’re out there, doing my bidding. Every time someone gets close, they’ll catch a whiff and wonder.”
James inhaled deeply, the musk filling his senses, heightening his arousal. It was overpowering, almost dizzying, a scent that would linger in his wake, marking him as something provocative, even if his appearance was demure. He nodded, his voice barely above a whisper. “Yes, Claire.”
She handed him the list again, along with a small black purse that matched the heels. “Keys are in there, along with your wallet—feminine, of course. Don’t forget to hike up that skirt when you climb into the truck. I want you to feel every inch of that plug as you sit.” Her fingers trailed down his arm, a possessive touch that sent shivers through him. “Go on, now. And remember, you’re mine out there.”
With a final glance in the mirror, James turned toward the door. The heels clicked with each step, the sway in his hips more pronounced now that he was moving with purpose. The tail brushed against his stockings, the plug a constant presence, filling him, teasing him. He descended the stairs carefully, gripping the railing, the perfume wafting around him like a cloud.
Outside, the summer air was warm, the sun casting long shadows across the driveway. His truck sat there, a rugged contrast to his current attire—a large pickup, high off the ground, requiring a step up to enter. James approached it, his heart pounding. He hiked the pencil skirt up slightly, the fabric bunching around his thighs, exposing more of his stockinged legs to the breeze. The tail swayed freely for a moment, tickling his skin, before he grabbed the handle and pulled himself up.
As he settled into the seat, the plug drove deeper into him, the sudden pressure eliciting a sharp gasp. It stretched him further, the fullness intensifying, sending a wave of pleasure-pain through his body. He shifted, trying to find a comfortable position, but every movement only heightened the sensation. The tail draped over the seat, its silicone strands brushing his calves. He closed the door, his breath coming in short bursts, the musky perfume filling the cab, making the space feel intimate, charged.
He started the engine, the rumble vibrating through the seat, amplifying the plug’s presence. Glancing in the rearview mirror, he saw his reflection—lips painted, eyes shadowed, wig perfectly in place. He looked like a woman on a mission, but inside, he was James, submissive and eager. With a deep breath, he pulled out of the driveway, heading toward his first stop: the post office.
The drive was short, but every bump in the road jolted the plug, making him clench around it, the tail swaying with the motion. The heels made accelerating and braking a deliberate act, the sway in his walk translating to a careful poise behind the wheel. The perfume lingered, a constant reminder of Claire’s words—extra slutty. He wondered if others would notice, if the scent would draw eyes or comments.
By the time he reached the post office, the sexual frustration had built to a low, constant hum. Every step, every shift of his weight, sent a jolt through him, the plug pressing against sensitive nerves, the tail teasing his skin. He stood in line, clutching the clutch, his lips parted slightly as he fought to keep his composure. The wig’s curls brushed his shoulders, the breast forms giving him a silhouette that drew subtle glances. He felt exposed, yet the act of passing as her—Claire’s perfect creation—filled him with a strange pride.
Pulling into the post office parking lot, James felt a surge of nervousness. The lot was half-full, people coming and going with packages and envelopes. He parked, turning off the engine, and sat for a moment, gathering his courage. His hands trembled slightly as he grabbed the two packages from the passenger seat—small boxes Claire had prepared, addressed and ready to ship. He hiked the skirt up again to step down, the plug shifting as he landed, heels clicking on the asphalt.
Striding toward the entrance, he focused on his gait—the subtle sway Claire had engineered with the heels. It made him feel feminine, vulnerable, each step a reminder of his role. The tail tickled his legs, hidden beneath the skirt, but he could feel it moving, a secret that heightened his anxiety. The musky perfume trailed behind him, and he wondered if the breeze carried it to others.
Inside, the post office was cool, the air humming with the sounds of stamps and scales. A line of three people waited at the counter, and James joined them, packages clutched to his chest, the breast forms pressing against the blouse. His heart raced, palms sweaty. He avoided eye contact, staring at the floor, the heels making him stand taller, more poised.
The line moved slowly. The first customer argued about postage rates, their voice echoing slightly. James shifted his weight, the plug pressing deeper, a whimper nearly escaping his lips. He bit down, focusing on the scent of the perfume, which now seemed even stronger in the enclosed space. Did the person in front of him notice? A middle-aged woman with a stack of letters glanced back, her eyes flicking over him briefly. James smiled nervously, hoping it looked natural.
Finally, it was his turn. He approached the counter, heels clicking loudly in the quiet. The desk clerk, a burly man in his fifties with a name tag reading “Frank,” looked up. “Morning, ma’am. What can I do for you?”
James’s throat tightened at the “ma’am,” a mix of thrill and terror. He placed the packages on the counter. “Just need to ship these,” he said, his voice soft, pitched higher as Claire had instructed during practice sessions.
Frank nodded, weighing the first package on the scale. “Where to?” he asked, typing into the computer.
“Addresses are on them,” James replied, watching as Frank scanned the labels. The scale beeped, numbers flashing. James felt exposed, the wig’s curls brushing his shoulders, the makeup feeling like a mask that could crack at any moment.
“First one to California, priority mail?” Frank confirmed.
“Yes, please.”
Frank processed it, printing a label and affixing it. The second package followed, destined for New York. James stood there, waiting, the plug a throbbing presence, the tail’s strands teasing his thighs. Every second stretched, his mind racing. What if Frank noticed the sway in his hips? The perfume? He shifted again, the heels making a soft scuff.
“That’ll be $18.75 for both,” Frank said, sliding the packages aside.
James fumbled in the purse for the wallet, pulling out cash—Claire had insisted on no cards that might reveal his name. He handed over a twenty, receiving change. “Thank you,” he murmured, taking the receipt.
“Have a nice day, ma’am,” Frank said, already turning to the next customer.
James turned away, relief washing over him. He strode out, the sway in his hips more confident now, the heels clicking triumphantly. The plug shifted with each step, a reward of sorts, the fullness sending sparks of pleasure. Outside, the sun warmed his skin, the perfume mingling with the fresh air.
Back at the truck, he hiked the skirt up once more, climbing in. The plug drove deep again as he sat, eliciting a soft moan that echoed in the cab. He started the engine, the vibration humming through him, amplifying everything—the arousal, the submission, the lingering scent. The post office was done; next was the dry cleaners.
The drive to the dry cleaners was a few miles away, through suburban streets lined with shops and houses. James gripped the wheel, his mind replaying the post office encounter. The “ma’am” had been affirming, a small victory in this game of Claire’s. But the nervousness lingered, building anticipation for the next stop. The tail swayed with the truck’s motion, brushing his legs, a constant tickle that kept him on edge.
Traffic was light, but each stoplight meant sitting still, the plug pressing insistently. He adjusted in the seat, the leather creaking, the breast forms shifting slightly. The wig felt warm, the makeup intact—he checked in the mirror at a red light. A car pulled up beside him, the driver a young woman who glanced over. Did she see through him? The light turned green, and he accelerated, the heels pressing the pedal with care.
As he approached the dry cleaners, a small strip mall shop called “Spotless Cleaners,” his pulse quickened again. This would be different—picking up, not dropping off, but still an interaction. Claire’s garments waited, pressed and ready. He parked, taking a deep breath, the musky perfume filling his lungs. Hiking the skirt, stepping down, the ritual repeated, the plug reminding him of his place.
But that was for the next leg of his journey. For now, the errands continued, each one a step deeper into submission.
Just a Couple More Stops
James pulled into the parking lot of Spotless Cleaners, the truck’s engine humming to a stop as he scanned the storefront. The small shop was tucked between a coffee house and a pharmacy, its sign faded but welcoming in the midday sun. His hands gripped the steering wheel a moment longer than necessary, the musky perfume still thick in the cab, mingling with the faint scent of leather seats. The post office had been a success—a small victory in this elaborate game Claire had orchestrated—but the dry cleaners felt like another hurdle, another chance for scrutiny.
He hiked the pencil skirt up slightly, the fabric sliding over his stockinged thighs, and stepped down from the truck. The three-inch block heels clicked against the pavement, enforcing that subtle sway in his hips as he walked. The plug shifted with the motion, a deep wiggle that made him pause, breath catching in his throat. It was impossible to ignore, the fullness pressing against him, the silicone tail tickling the backs of his legs like a secret whisper. He smoothed the skirt down, self-conscious of the sensation, knowing no one around him could possibly guess at the intrusion hidden beneath his feminine facade. To the world, he was just a woman running errands—poised, perhaps a bit hurried—but inside, he was a bundle of nerves and arousal.
The door to the dry cleaners chimed as he entered, a soft bell announcing his arrival. The air inside was warm, scented with starch and faint chemicals, a stark contrast to the heavy musk clinging to his skin. A young woman behind the counter looked up, her smile professional. “Ticket?” she asked, her eyes flicking over him briefly.
James rummaged in the purse, pulling out the slip Claire had tucked inside. “Here,” he said, his voice pitched softly, feminine. He placed it on the counter, the breast forms shifting slightly under the blouse as he leaned forward. The plug wiggled again, a reminder that made his cheeks flush beneath the makeup. He stood straight, heels grounding him, the tail’s strands brushing his calves.
The clerk disappeared into the back, hangers rattling as she retrieved the items—a few blouses and a dress of Claire’s, neatly pressed and covered in plastic. James waited, shifting his weight from one foot to the other. The movement caused the plug to press deeper, a jolt that sent a shiver up his spine. He bit his lip, the berry red lipstick a barrier against any sound escaping. No one knew, he reminded himself. The clerk returned, oblivious, ringing up the total.
“That’ll be $42.50,” she said, her gaze neutral.
James paid with cash again, avoiding any trace of his real identity. As he took the garments, their plastic crinkling, he caught a whiff of his perfume—strong, slutty, as Claire had intended. Did the clerk notice? She didn’t react, but James felt exposed, the scent a beacon drawing subtle attention. He thanked her quietly and turned, the heels clicking as he exited, hips swaying involuntarily.
The tail swayed as he turned to leave, a secret only he knew, its strands tickling his thighs like a whispered command.
The pencil skirt hugged his thighs, restricting his stride just enough to make him conscious of every movement. The stockings whispered against his skin, the lace panties teasing his manhood with every step. But it was the plug and its tail that dominated his thoughts—the fullness inside him, the soft tickle of silicone against his legs, a constant reminder of Claire’s control.
Back at the truck, he hung the dry cleaning on the hook in the cab, then climbed in. The skirt hiked up, and as he sat, the plug drove deeper once more, eliciting a soft whimper. The fullness was overwhelming now, building on the earlier sensations, the tail draping over the seat like a teasing appendage. He started the engine, the vibration rumbling through him, amplifying every shift. One more stop: the grocery store. The list in his purse felt heavier now, a promise of prolonged exposure.
The drive to the supermarket was longer, traffic building as lunchtime approached. James navigated the streets carefully, the heels making pedal work deliberate. Every red light meant sitting still, the plug a constant pressure, the sexual frustration simmering beneath the surface. By the time he pulled into the bustling parking lot of the local grocery chain, it had built to a low, constant hum—a background thrum of need that colored every thought.
At the grocery store, he moved carefully, the plug shifting slightly as he reached for items on the list. The tail brushed against his stockings, hidden beneath the skirt but ever-present in his mind. He caught a few curious glances, but whether they were admiring or suspicious, he couldn’t tell. His cheeks burned beneath the blush Claire had applied, but he pressed on, her instructions echoing in his head.
He parked near the back, away from prying eyes, and repeated the ritual: skirt up, step down, heels on asphalt. The sway was more pronounced now, fatigue from the heels making his movements slower, more deliberate. The plug wiggled with each step toward the entrance, the tail tickling relentlessly, a sensory overload that made him hyper-aware of his body. Shoppers streamed in and out, carts clattering, but no one gave him more than a passing glance. He was passing—Claire’s perfect creation—and that knowledge filled him with a strange pride, even as the self-consciousness gnawed at him.
Inside, the store was a cacophony of beeps, announcements, and chatter. Fluorescent lights buzzed overhead, illuminating aisles stocked with colorful packaging. James pulled out the list, his eyes widening slightly. It was longer than he’d anticipated—produce, dairy, pantry staples, even some specialty items Claire must have added for her own amusement. No rushing through this, not in these heels. He grabbed a cart, the wheels squeaking as he pushed it forward, the breast forms bouncing lightly with the motion.
He started in the produce section, reaching for apples and bananas. The stretch caused the plug to shift, a deep press that made his knees weaken. He paused, pretending to inspect a pear, but really steadying himself against the wave of sensation. The wig’s curls brushed his shoulders, a soft caress that reminded him of his transformed state. A man nearby glanced over, his eyes lingering on the silhouette the breast forms created, but he moved on without a word. Close enough to suspect? James wondered, but the interaction was nil, leaving him to his internal turmoil.
Moving methodically, he couldn’t hurry. The heels enforced a slow pace, each step a sway of hips, the skirt brushing his thighs, the tail tickling like feathers on skin. In the dairy aisle, grabbing yogurt and milk, the cold air from the fridges made his nipples harden against the bra, another layer of exposure. The plug wiggled incessantly, pressing against sensitive nerves, building that hum into something more urgent. He felt the lace panties teasing his manhood, the openness in the back allowing the tail to sway freely beneath the skirt.
By the time he reached the canned goods, sweat dampened his brow, the makeup holding but his composure fraying. The list dragged on—spices, bread, cleaning supplies. Every bend or reach sent jolts through him, the frustration mounting. A woman nearby, an elderly lady with a walker, asked him to pass a box of cereal from a high shelf. “You’re so tall in those heels, dear,” she said with a chuckle.
James obliged, the action stretching him, the plug driving deep. “Happy to help,” he replied, voice steady despite the internal chaos. She thanked him, no suspicion, just gratitude. It bolstered him, that pride swelling again—he was navigating this world as her, unseen for what he truly carried.
The bakery section tempted with fresh scents, but he stuck to the list, adding bagels. The cart grew heavy, pushing it a workout in the heels. In the frozen foods, the chill amplified the goosebumps on his legs, the stockings no barrier. The tail teased mercilessly, the plug a wiggling intruder that made every aisle feel like an eternity.
Finally, the last item: a bottle of olive oil from the international aisle. James sighed inwardly, the sexual frustration now a palpable ache. Every step sent a jolt, the constant hum a symphony of need. He headed to checkout, opting for self-service to avoid more eyes, more chances for conversation laced with perfume.
The line for self-checkout was moderate, a few people ahead. James stood, clutching the purse, his lips parted slightly as he breathed through the sensations. The wig’s curls tickled his shoulders, the breast forms drawing subtle glances from a couple in front—a quick look, then away. He felt exposed, the makeup a thin veil, but the act of passing filled him with that odd pride. The plug pressed with every shift, the tail teasing, his mind a haze of arousal and focus.
When his turn came, scanning items was methodical, but it took longer than wished. The machine beeped erratically, requiring overrides for produce weights. He bagged groceries carefully, the bending and lifting wiggling the plug anew, his hands trembling slightly. No interactions, just the impersonal screen, but the frustration built, the hum insistent.
Paid and done, he pushed the cart to the truck, heels clicking, hips swaying. The parking lot felt endless, but he loaded the bags under the bed cover, securing them against shifting. Climbing in one final time, he hiked the skirt, settling into the seat with a sigh of relief escaped as the plug settled, though still deep and full. The engine started, vibration a familiar tormentor, but home beckoned—Claire waiting, the errands conquered.
As he drove, the sun dipped lower, casting golden light through the windshield. The musky perfume faded slightly, but the sensations lingered, a promise of reward or continuation. James felt a mix of exhaustion and eagerness, ready to return to her dominion.
An Unexpected Detour
The hum of the truck’s engine was a steady companion as James drove through the suburban streets, the late afternoon sun casting long shadows across the dashboard. The grocery bags were safely stowed under the bed cover, the dry cleaning hung neatly in the cab, and the post office receipt was tucked into the black clutch purse beside him. His body thrummed with a low, constant arousal, the plug shifting with every subtle movement, the silicone tail tickling the backs of his stockinged legs. The musky perfume still clung to him, its heavy amber and vanilla notes filling the cab, a reminder of Claire’s command to exude a provocative edge. The block heels had enforced a feminine sway in his hips all day, and now, as he navigated the familiar route home, he felt both exhausted and exhilarated, a strange pride in having passed as her—Claire’s perfect creation—through every errand.
Halfway home, the truck idling at a stoplight, his phone buzzed in the purse. James glanced at the light—still red—and fished out the device, his manicured fingers brushing against the lace of the clutch. The screen lit up with a text from Claire, the notification sending a jolt through him that rivaled the plug’s constant pressure. He unlocked the phone, heart pounding, and read her message: One more errand, darling. Stop by Bella’s Boutique on Maple. Pick up the package I ordered. No questions. Be my good girl.
His breath caught, the words sinking in. Another errand? Now? The light turned green, and he eased the truck forward, his mind racing. Bella’s Boutique was a small, upscale shop known for lingerie and women’s accessories—a place he’d never entered as James, let alone in this transformed state. The plug wiggled as he shifted in the seat, the tail brushing his calves, amplifying the nervous excitement building in his chest. Claire’s command was clear, her tone in the text as firm as her voice had been that morning. He couldn’t refuse, not when the day had been about proving his submission, his willingness to embody her vision.
He turned the truck toward Maple Street, the route adding a few miles to his journey home. The heels made driving a deliberate act, each press of the pedal a reminder of his altered gait. The pencil skirt hugged his thighs, the blouse shifting over the breast forms, their weight a constant anchor to his feminine persona. The wig’s chestnut curls brushed his shoulders, and he caught a glimpse of himself in the rearview mirror—lips painted berry red, eyes shadowed, a woman staring back. The musky perfume seemed to pulse with his heartbeat, its scent a bold declaration he couldn’t escape.
As he approached Bella’s Boutique, the parking lot was mercifully quiet, only a few cars scattered near the entrance. The shop’s facade was elegant, with frosted glass windows and a sleek sign in cursive script. James parked, his hands trembling slightly as he turned off the engine. The plug pressed deeper as he sat still, a wave of sensation that made him bite his lip to stifle a moan. He hiked the skirt up to step down, the tail swaying freely for a moment, tickling his legs before he smoothed the fabric back into place. The heels clicked on the asphalt, enforcing that sway in his hips as he walked toward the entrance, the clutch clutched tightly in one hand.
Inside, the boutique was a sensory overload—soft lighting, racks of delicate lingerie, and shelves lined with perfumes and accessories. The air was scented with rose and lavender, a lighter contrast to the heavy musk clinging to him. A woman in her thirties, dressed in a chic black dress, looked up from behind the counter. Her name tag read “Lila,” and her smile was warm but professional, her eyes flicking over James with a practiced assessment.
“Welcome,” Lila said, her voice smooth. “Can I help you find something?”
James swallowed, his throat tight. “I’m here to pick up a package,” he said, pitching his voice soft and feminine as Claire had taught him. “Under the name Claire Thompson.”
Lila nodded, tapping at a tablet. “Let me check.” She disappeared into a back room, leaving James standing in the middle of the boutique. He shifted his weight, the heels making his calves ache slightly, the plug wiggling with the motion. The tail teased his stockings, a secret no one here could know, but the sensation made him hyper-aware of his exposure. A customer browsed nearby—a woman in her twenties, flipping through a rack of silk camisoles. She glanced at James, her eyes lingering on his silhouette, the breast forms giving him a convincing feminine curve. Did she suspect? Her gaze returned to the rack, and James exhaled, the moment passing.
Lila returned with a small, discreet black box tied with a red ribbon. “Here it is,” she said, handing it to him. “Claire’s order. Would you like me to ring it up, or is it prepaid?”
“Prepaid,” James said quickly, remembering Claire’s instructions. He took the box, its weight light but its presence heavy with implication. What was inside? Lingerie? Something more intimate? He didn’t dare ask, not here, not now.
“Thank you,” he said, tucking the box into his purse. The clutch barely accommodated it, the ribbon peeking out. Lila smiled again, her eyes lingering a moment longer than necessary. Did she catch the musky perfume? James felt a flush creep up his neck, the makeup hiding it but not the self-consciousness. He turned, heels clicking, hips swaying as he exited, the tail tickling with every step.
Back in the truck, he set the purse on the passenger seat, the black box a silent taunt. Climbing in, he hiked the skirt once more, the plug driving deeper as he settled, a soft gasp escaping his lips. The tail draped over the seat, its strands brushing his legs, the sensation now a familiar torment. He started the engine, the vibration amplifying the plug’s presence, the sexual frustration a constant hum that had grown sharper with each errand. The boutique had been intimate, exposing, and the knowledge that he’d passed—again—filled him with that strange mix of pride and vulnerability.
The drive home resumed, but the new errand had heightened everything. The plug wiggled with every turn, every bump, pressing against sensitive nerves. The tail teased relentlessly, a tickle that kept his mind on Claire’s control. The musky perfume filled the cab, its slutty edge a constant reminder of her intent. He wondered about the box—what new command would it bring? The thought sent a shiver through him, the frustration building into an ache he couldn’t ignore.
Traffic was light now, the suburbs quieting as the day waned. James’s mind replayed the boutique encounter—Lila’s assessing gaze, the other customer’s glance. No one had questioned him, no one had seen through the facade, but the possibility lingered, especially with the perfume announcing his presence. Close enough, someone might suspect—a shadow of stubble beneath the foundation, a voice too low if he wasn’t careful. But Claire’s work was meticulous, the wig, makeup, and outfit a perfect disguise.
As he neared home, the anticipation of seeing Claire grew. Would she inspect the box first? Demand a report of his day? The plug and tail kept him grounded in his submission, each sensation a reminder of her dominance. He stopped at one last light, the engine idling, the plug pressing deep. He adjusted in the seat, the tail shifting, and checked the mirror. The woman staring back was tired but poised, lips parted slightly, eyes wide with a mix of exhaustion and eagerness.
The final stretch home was a blur, the truck’s rumble a backdrop to his thoughts. He pulled into the driveway, the familiar sight of their house a relief. Turning off the engine, he sat for a moment, the plug still, the tail draped over his legs. The black box in the purse seemed to pulse with possibility, a final test of his obedience. He hiked the skirt up one last time, stepping down, heels clicking on the concrete. The dry cleaning, groceries, and now the mysterious package—all completed, all under Claire’s command.
He gathered everything, the dry cleaning over one arm, the purse with the box in hand, and headed to the door. The plug wiggled as he walked, the tail tickling, the heels enforcing that sway. The musky perfume trailed behind, a final declaration of his role. He felt exposed, aroused, and utterly hers, the day’s errands a testament to his surrender.
When he finally returned home, the errands complete, Claire was waiting. She stood in the doorway, her arms crossed, her eyes gleaming with approval. “Well done,” she said, her voice warm but still laced with that commanding edge. She stepped closer, her fingers brushing the hem of his skirt, then trailing up to rest on his hip. “How did it feel, my darling? Knowing you were mine, every step of the way?”
James exhaled, his voice trembling with the weight of the day. “It was… intense,” he admitted, the plug still filling him, the tail still teasing. “I felt you with me, every moment.”
Claire’s smile widened, and she leaned in, her lips brushing his ear. “Good,” she whispered. “Because this is only the beginning.”
Her eyes gleamed, taking in his appearance, the packages, the purse. “Well done, my darling,” she said, her voice low and approving. “Let’s see what you’ve brought me.”
James handed her the purse, the black box inside, and stood, heart pounding, the plug and tail a constant reminder of his place. The errands were done, but the game, he knew, was far from over.
The Unveiling
The front door clicked shut behind James, the sound echoing softly in the quiet house. The evening sun had dipped low, casting a warm, golden hue through the windows, but the air inside felt charged, heavy with anticipation. His arms were laden with the day’s spoils: the dry cleaning draped over one shoulder, grocery bags clutched in his hands, and the black clutch purse—now holding the mysterious box from Bella’s Boutique—tucked under his arm. The three-inch block heels clicked against the hardwood floor as he made his way to the kitchen, each step sending a familiar wiggle through the plug nestled deep inside him. The silicone tail brushed against his stockinged legs, a constant tickle that had kept him on edge throughout the errands. The musky perfume clung to his skin, its amber and vanilla notes mingling with the faint jasmine scent that always seemed to linger in their home.
She led him upstairs to their bedroom, the familiar space now bathed in the soft glow of bedside lamps. The bed was neatly made, the curtains drawn, creating an intimate cocoon. Claire placed the purse on the dresser and carefully extracted the black box, tied with its red ribbon. James stood nearby, shifting slightly, the plug pressing deeper with the movement, eliciting a quiet gasp he couldn’t suppress.
Claire untied the ribbon with deliberate slowness, her eyes locked on his. The box opened to reveal tissue paper, which she peeled back to uncover the contents. First, a delicate, sheer nightgown in soft ivory lace, its fabric translucent and flowing, designed to skim the body in a teasing caress. Beneath it, a set of restraints—supple leather cuffs lined with velvet, connected by short chains, simple yet elegant in their purpose.
James’s breath hitched. The nightgown was beautiful, feminine, a step deeper into the persona she’d created for him. The restraints, though… they promised a loss of control that made his pulse race.
Claire held up the nightgown, letting it drape over her arm. “Exquisite, isn’t it? And these…” She dangled the restraints from her fingers. “Will ensure you stay exactly where I want you.” She set them aside and turned to him, her expression softening with praise. “You did so well today, James. Or should I say, my lovely Jasmine? You passed flawlessly—those glances at the post office, the dry cleaners, even in the grocery store. No one suspected a thing. You were just another woman running errands, hips swaying in those heels, the perfume drawing subtle looks.”
He flushed, the memory of the day flooding back. The nervousness at each stop, the constant awareness of the plug and tail, the fear of discovery mixed with the thrill of success. “It was… intense,” he admitted, his voice trembling slightly. “I kept thinking someone would notice something off.”
“But they didn’t,” Claire said, stepping closer, her hands resting on his hips. “You were perfect. And that scent… oh, I can still smell it on you. Musky, slutty, just as I intended. Imagine the clerk at the boutique catching a whiff, wondering why this poised woman smelled like pure desire. Or the man in line at the grocery store, inhaling deeply as you passed, his mind wandering to forbidden thoughts.”
James shivered, arousal stirring despite the lingering nervousness. The public exposure had been exhilarating, but it left him raw, vulnerable. Part of him craved the safety of home, yet another part yearned for more of her control.
“Now,” Claire said, her tone shifting to command, “strip out of those clothes and put on the nightgown. Keep the plug and tail in place—they’re staying for now.”
James obeyed, his fingers fumbling slightly with the buttons of the blouse. The fabric slipped off, revealing the full-coverage black bra and breast forms. He unzipped the pencil skirt, letting it pool at his feet, the stockings and lacy panties exposed. The open back of the panties framed the tail, its silicone strands hanging down like a provocative accessory. He stepped out of the heels, the relief momentary, then removed the bra, the forms heavy in his hands before he set them aside. Naked except for the stockings, panties, wig, and makeup, he felt utterly exposed.
Claire watched, her eyes dark with desire. She handed him the nightgown, and he slipped it on, the sheer fabric cascading over his body like a second skin. It was short, ending mid-thigh, the lace teasing his skin, translucent enough to hint at what lay beneath. The tail peeked out from under the hem, a bold contrast to the delicate garment.
“Beautiful,” Claire murmured, circling him. “My perfect submissive.” She took his hand and led him to the bed, where she had him sit on the edge. Picking up the restraints, she fastened the cuffs around his wrists, the velvet soft against his skin, the leather firm. The chains were short, allowing limited movement once connected.
“Lie back,” she instructed, and he did, scooting up the bed until his head rested on the pillows. Claire straddled him briefly to secure the chains to the headboard, binding his wrists above his head. The position stretched him out, the nightgown riding up slightly, the tail splaying across the sheets. The plug shifted as he settled, a deep fullness that made him arch slightly.
Bound now, James tested the restraints, the gentle tug confirming his helplessness. Arousal surged through him, his manhood straining against the lace panties, but mingled with it was a thread of nervousness. The day’s events replayed in his mind—the stares, the interactions, the constant fear of being outed. What if someone had noticed the sway of his hips was a bit too forced? Or caught a glimpse of the tail’s movement under the skirt? The vulnerability of being seen, judged, exposed in public clashed with the safety of this private surrender.
Claire noticed his distant gaze and smiled, settling beside him on the bed. Her fingers traced patterns on his thigh, inching toward the hem of the nightgown. “You’re thinking about today, aren’t you? All those people, oblivious to the secret you carried. The plug filling you, the tail teasing your legs, while you smiled and paid for groceries like any other woman.”
James nodded, his breath shallow. “It was scary… but exciting. I kept imagining what they’d think if they knew.”
“Oh, but that’s the thrill,” Claire said, her voice a whisper as she leaned in, her lips brushing his ear. “And the perfume—god, that musk. Picture the woman at the dry cleaners, inhaling as you handed over the ticket. Did she wonder why you smelled so intoxicating, so ready? Or the young clerk at the boutique, her cheeks flushing as the scent hit her, imagining you in something from their stock, legs spread, eager.”
Her words painted vivid pictures, heightening his arousal even as the nervousness lingered. The internal conflict raged—part of him wanted to hide, to shed the persona and return to normalcy, but the deeper part craved this deepening submission. Claire’s psychological dominance was masterful, weaving his fears into fuel for his desire.
She trailed her hand higher, fingers ghosting over the lace panties, feeling his hardness. “You’re so responsive, my love. All day, building that frustration, and now here you are, bound for me.” She tugged gently at the tail, the motion jostling the plug, drawing a moan from him. “I think you deserve a reward…”
The Reward
Claire’s fingers lingered at the hem of the sheer ivory nightgown, tracing lazy circles along the lace edge that skimmed James’s mid-thigh. The fabric was so delicate, almost ethereal, clinging to his skin like a lover’s whisper, translucent enough to reveal the outline of the lacy black panties beneath. The silicone tail from the plug dangled teasingly from under the hem, its soft strands splayed across the sheets like an invitation. James—Jasmine, as Claire had dubbed him for the evening—lay bound to the headboard, his wrists secured in the velvet-lined leather cuffs, the short chains allowing only the slightest wiggle room. He couldn’t reach out, couldn’t touch her, couldn’t control a single thing. The plug nestled deep inside him, a constant, throbbing fullness that had been his companion all day, shifting with every breath, every subtle arch of his back. The wig’s chestnut curls framed his face, the makeup still flawless despite the day’s exertions, his berry-red lips parted in anticipation.
She hovered over him, her silk robe loosely tied, revealing glimpses of her own curves beneath. Her dark eyes gleamed with a mix of pride and hunger, appraising her creation. “You’ve been such a good girl today, Jasmine,” she murmured, her voice a sultry purr that sent shivers down his spine. “Running all those errands for me, dressed so perfectly, with that little secret tucked away inside you. The plug filling you up, the tail teasing your legs… and no one suspected a thing. You were my flawless submissive, weren’t you?”
James nodded, his voice a breathy whisper. “Yes, Claire. I… I did it all for you.” The words came out soft, tinged with the higher pitch he’d practiced, but underneath was the raw vulnerability of his true self. The day’s events replayed in flashes—the post office clerk’s casual “ma’am,” the subtle glances at the grocery store, the musky perfume drawing invisible attention. It had been terrifying, exhilarating, a constant edge of exposure that left him aching with unmet need. Now, bound and helpless, that ache pulsed stronger, his manhood straining against the sheer lace of the panties, desperate for release after hours of denial.
Claire’s smile widened, predatory yet affectionate. She leaned in closer, her breath warm against his neck as she trailed her fingers up his thigh, stopping just short of the nightgown’s hem. “And you deserve a reward for that, don’t you? But first… I think I’ll make you wait a little longer. Build that frustration until you’re begging.” Her hand ghosted over the fabric, brushing the tail’s strands aside, then pressing lightly against the base of the plug through the open back of the panties. The pressure sent a jolt through him, the plug wiggling deeper, stimulating nerves that had been sensitized all day. James gasped, his hips bucking involuntarily, the chains rattling softly against the headboard.
“Oh, you like that, don’t you?” Claire teased, her fingers circling the base now, tugging gently at the tail. Each pull shifted the plug inside him, a delicious stretch that bordered on overwhelm. The silicone strands swayed, tickling his inner thighs, heightening the sensation. She watched his face, drinking in every twitch, every parted-lip exhale. “All day, every step you took—climbing into that truck, walking through those stores—the plug was there, reminding you of me. Filling you, owning you. And the tail… god, imagining it brushing your stockings under that skirt, hidden but so very present. Did it make you hard, Jasmine? Did it make you wish you could touch yourself right there in the parking lot?”
James whimpered, nodding fervently. “Y-yes… it was torture. Every bump in the road, every shift… I couldn’t stop thinking about you.” His body trembled, the nightgown’s lace rubbing against his skin like a thousand tiny caresses. The restraints held him firm, his arms stretched above his head, leaving him utterly exposed. Claire’s dominance was absolute, her touch both reward and torment. She leaned down, her lips brushing his collarbone through the sheer fabric, then trailing kisses lower, over the flat plane of his chest where the nightgown clung. Without the breast forms, his body was more his own now, yet the feminine attire and wig kept him immersed in the role—Jasmine, her perfect sissy, at her mercy.
She continued the tease, her hands exploring with deliberate slowness. One finger traced the outline of his straining erection through the lace panties, the front panel sheer and confining, holding him captive. “Look at you, so eager,” she whispered, pressing her palm against him, feeling the heat and hardness. James moaned, his hips lifting toward her touch, but she pulled back just enough to deny full contact. “Not yet. Tell me more about your day. How did it feel at the boutique, picking up that package? Smelling like a slut, with the tail swaying under your skirt?”
“It was… humiliating, but hot,” he admitted, his voice cracking. “The clerk looked at me funny, like she could smell the perfume. And the tail… it kept moving, teasing me. I thought someone might see.” The confession fueled his arousal, the vulnerability making him throb harder against the lace. Claire rewarded him with a firmer stroke, her hand cupping him through the fabric, but still not freeing him. She alternated pressure on the plug’s base, wiggling it in rhythm with her touches, creating a symphony of sensations that had him writhing.
“Good girl,” she praised, her free hand slipping under the nightgown to pinch his nipple lightly, rolling it between her fingers. The dual assault—plug shifting inside, hand teasing outside—built the pressure inexorably. James’s breaths came in ragged gasps, his body arching as much as the restraints allowed. Sweat beaded on his forehead, smudging the makeup slightly, but Claire didn’t mind; it only added to his disheveled, desperate allure. She kissed his neck, nipping at the skin, then whispered, “You’re mine, Jasmine. All mine. And tonight, I’m going to make you feel every bit of that.”
After what felt like an eternity of edging touches—strokes that promised more but delivered just enough to keep him on the brink—Claire finally relented. Her fingers hooked into the waistband of the panties, pulling the front down slowly, exposing his cock to the cool air. It sprang free, hard and eager, glistening with pre-cum from the day’s pent-up frustration. The open back of the panties remained in place, framing the plug and tail, keeping that intrusion secure. “There it is,” Claire murmured, her eyes darkening with lust. “Your sissy cock, waiting all day for this. So hard for me, isn’t it?”
James could only nod, his eyes locked on hers, pleading silently. The release from confinement was a relief, but the teasing had left him hypersensitive, every brush of air a torment. Claire wrapped her hand around him, stroking languidly, her grip firm but slow. “Feel that? That’s your reward starting. But I’m in control, remember? You’ll come when I say.”
She shifted her position, swinging one leg over him to straddle his thighs, her silk robe falling open to reveal her naked body beneath. Her warmth pressed against him, her core hovering just above his freed erection, teasing without contact. James strained against the cuffs, wanting to touch her, to pull her down, but the chains held fast. The plug shifted with his movements, adding to the overload. Claire leaned forward slightly, her breasts brushing his chest through the nightgown, the lace a barrier that heightened the friction. “Patience, my love,” she said, guiding the tip of his cock to her entrance, letting it brush against her wetness but not entering yet.
Slowly, agonizingly, she lowered herself onto him, inch by inch. The sensation was exquisite—her tight heat enveloping him, contrasting with the fullness of the plug inside. James groaned, his head falling back against the pillows, the wig’s curls splaying out. “Claire… please…” The tail tickled his legs as she settled fully, her hips grinding in small circles, building the rhythm. She rode him with control, rising and falling at a pace that brought him closer to the edge with each thrust, the plug wiggling in sync, doubling the pleasure.
As he approached climax, his breaths turning to pants, his body tensing, Claire paused, stilling completely. She sat atop him, his cock buried deep inside her, but unmoving. “Not yet,” she commanded, her voice firm. James whimpered, bucking his hips futilely, the restraints and her weight holding him in place. The edge was torturous, the plug’s pressure amplifying the denial. She watched him squirm, a smile playing on her lips, then leaned forward fully, her breasts pressing against his chest, the nightgown’s lace rubbing between them. Her face hovered above his, eyes locked.
“Now,” she whispered, crashing her lips against his in a passionate kiss. Her tongue invaded his mouth, claiming him as she began to move again, driving down hard. The kiss was fierce, berry lipstick smearing between them, her hands tangling in the wig’s curls. She thrust deeply, grinding against him, the motion jostling the plug and tail, sending him over the brink. Ecstasy washed over James—Jasmine—in waves, his release filling her as he cried out into the kiss, his body convulsing in helpless pleasure. The dual sensations—her around him, the plug within—created an overload that left him trembling, lost in the role, utterly hers.
Claire followed soon after, her own climax rippling through her, clenching around him as she moaned against his lips. They collapsed together, her body draping over his, breaths mingling in the afterglow. She reached up to unfasten the cuffs, freeing his wrists, and he immediately wrapped his arms around her, holding her close. The plug remained, a gentle reminder, but the urgency had faded into contentment.
After a few moments of silent cuddling, Claire rolled off him, the nightgown sticking slightly with sweat. “Let’s clean up,” she said softly, helping him to his feet. In the adjoining bathroom, under the warm glow of the vanity lights, she gently removed the plug and tail, washing them and him with care. James stood, still in the nightgown and wig, watching as she wiped away the smeared makeup with a soft cloth, her touches tender now. “You were incredible today,” she said, meeting his eyes in the mirror. “The errands, the boutique… you embraced it all.”
He smiled, leaning into her. “It was scary, but… fun. The thrill of almost being caught, feeling so exposed. And now, this.” They returned to the bed, cuddling under the sheets, her head on his chest. “What about future games? More errands? Maybe something riskier?”
Claire chuckled, tracing patterns on his skin. “Oh, definitely. Imagine a dinner out, or a shopping trip where I make you try on more outfits. The fun is just beginning, my Jasmine.” They lay there, reflecting on the day’s adventures—the transformation, the public submission, the intimate reward—knowing their bond was stronger, their explorations endless.